NCS-382

NCS-382

Names
IUPAC name (2E)-(5-hydroxy-5,7,8,9-tetrahydro-6H-benzo[a][7]annulen-6-ylidene ethanoic acid
Identifiers
CAS Number	131733-92-1
3D model (Jmol)	Interactive image
ChemSpider	4730868
MeSH	NCS-382
PubChem	5875451
InChI InChI=1S/C13H14O3/c14-12(15)8-10-6-3-5-9-4-1-2-7-11(9)13(10)16/h1-2,4,7-8,13,16H,3,5-6H2,(H,14,15)/b10-8+ Key: UADPGHINQMWEAG-CSKARUKUSA-N InChI=1/C13H14O3/c14-12(15)8-10-6-3-5-9-4-1-2-7-11(9)13(10)16/h1-2,4,7-8,13,16H,3,5-6H2,(H,14,15)/b10-8+ Key: UADPGHINQMWEAG-CSKARUKUBJ
SMILES c1ccc2c(c1)CCC/C(=C\C(=O)O)/C2O
Properties
Chemical formula	C13H14O3
Molar mass	218.248
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

NCS-382 is a moderately selective antagonist for the GHB receptor.^[1][2] It blocks the effects of GHB in animals and has both anti-sedative and anticonvulsant effects.^[3][4][5] It has been proposed as a treatment for GHB overdose in humans as well as the genetic metabolic disorder succinic semialdehyde dehydrogenase deficiency (SSADHD), but has never been developed for clinical use.^[6]

References

1. Castelli MP, Pibiri F, Carboni G, Piras AP (2004). "A review of pharmacology of NCS-382, a putative antagonist of gamma-hydroxybutyric acid (GHB) receptor" (pdf). CNS Drug Reviews. 10 (3): 243–260. doi:10.1111/j.1527-3458.2004.tb00025.x. PMID 15492774.
2. Ticku MK, Mehta AK (October 2008). "Characterization and pharmacology of the GHB receptor". Annals of the New York Academy of Sciences. 1139: 374–385. doi:10.1196/annals.1432.048. PMID 18991884.
3. Maitre M, Hechler V, Vayer P, Gobaille S, Cash CD, Schmitt M, Bourguignon JJ (Nov 1990). "A specific gamma-hydroxybutyrate receptor ligand possesses both antagonistic and anticonvulsant properties". Journal of Pharmacology and Experimental Therapeutics. 255 (2): 657–563. PMID 2173754.
4. Schmidt C, Gobaille S, Hechler V, Schmitt M, Bourguignon JJ, Maitre M (Oct 1991). "Anti-sedative and anti-cataleptic properties of NCS-382, a gamma-hydroxybutyrate receptor antagonist". European Journal of Pharmacology. 203 (3): 393–297. doi:10.1016/0014-2999(91)90896-X. PMID 1773824.
5. Colombo G, Agabio R, Bourguignon J, Fadda F, Lobina C, Maitre M, Reali R, Schmitt M, Gessa GL (Sep 1995). "Blockade of the discriminative stimulus effects of gamma-hydroxybutyric acid (GHB) by the GHB receptor antagonist NCS-382". Physiology and Behaviour. 58 (3): 587–590. doi:10.1016/0031-9384(95)00086-X. PMID 8587968.
6. Gupta M, Greven R, Jansen EE, Jakobs C, Hogema BM, Froestl W, Snead OC, Bartels H, Grompe M, Gibson KM (Jul 2002). "Therapeutic intervention in mice deficient for succinate semialdehyde dehydrogenase (gamma-hydroxybutyric aciduria)" (pdf). Journal of Pharmacology and Experimental Therapeutics. 302 (1): 180–187. doi:10.1124/jpet.302.1.180. PMID 12065715.